Methyl Thioglycolate → Methyl {[bis(4-fluorophenyl)methyl]sulfanyl}acetate

Participants

Reaction Steps

A slurry of ρ-toluenesulfonic acid monohydrate (108 mg, 0.57 mmol) and activated 3 Å molecular sieves (300-500 mg) in 4 mL of toluene is stirred for 15 minutes. Methyl thioglycolate (265 mg, 2.50 mmol ) is then added followed by 4,4'-difluoro-benzhydrol (Aldrich) (500 mg, 2.27 mmol). The reaction is stirred for 2.5 hours at room temperature followed by heating at 50°-60° C. for 45 minutes. The mixture is diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, brine and dried over magnesium sulfate. Chromatography on silica gel, eluting with a gradient of 10% ethyl acetate in hexane to 20% ethyl acetate in hexane, provides methyl [[bis-(4-fluorophenyl)methyl]thio]acetate as a yellow oil in 50% yield.

Provenance & Evidence